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Search results; Over 1,000 homes in Madison

Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
25–30 Aug
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4.98 out of 5 average rating, 227 reviews
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds, 5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Home in Madison
Madison Bay Club House
3 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds, 4.5 bathrooms
5–10 Sept
4.99 out of 5 average rating, 143 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 249 reviews
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 189 reviews
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.99 out of 5 average rating, 222 reviews
Guest favourite
Home in Cambridge
The Sailor’s Shanty
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 104 reviews
Guest favourite
Home in Cambridge
Peaceful Historic House Near Water, with Hot Tub!
3 bedrooms, 3 beds, 1.5 bathrooms
18–23 Aug
4.94 out of 5 average rating, 185 reviews
Guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 689 reviews
Home in Madison
Madison Bay Retreat
2 bedrooms, 2 beds, 2 bathrooms
18–23 Aug
Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Cambridge
Waterfront Home w/ Pool, Hot Tub, Kayaks & More
5 bedrooms, 5 beds, 4 bathrooms
22–27 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Cambridge
The Mariner at Swan Cove Manor
5 bedrooms, 11 beds, 3.5 bathrooms
18–23 Aug
4.94 out of 5 average rating, 33 reviews
Home in Cambridge
Waterfront Cambridge Retreat/View Choptank River
3 bedrooms, 3 beds, 3.5 bathrooms
19–24 Aug
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